N-(1-acetyl-5-indolinyl)-2-chloroallylamine | 158942-44-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-(1-acetyl-5-indolinyl)-2-chloroallylamine
• 英文别名: 1-[5-(2-Chloroprop-2-enylamino)-2,3-dihydroindol-1-yl]ethanone
• CAS: 158942-44-0
• 化学式: C₁₃H₁₅ClN₂O
• 分子量: 250.728
• InChiKey: DIZWISIFXATGKV-UHFFFAOYSA-N

物化性质

• 沸点：
  501.2±50.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1-acetyl-5-indolinyl)-2-chloroallylamine 在 PPA 、 sodium hydride 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 3.5h， 生成 1-(1,3-Dimethyl-6,7-dihydropyrrolo[2,3-f]indol-5-yl)ethanone
  参考文献：
  名称：

  Synthesis, Biological Activity, and Molecular Modeling Studies of Selective 5-HT_2C/2B Receptor Antagonists

  摘要：

  The synthesis and biological activity are reported for a series of analogues of the previously published indole urea 2 (SB-206553), designed to probe the 5-HT2C receptor binding site. Small molecule modeling studies have been used to define a region in space which is allowed at the 5-HT2C receptor but disallowed at the 5-HT2A receptor. In a complementary approach, docking of 2 into our model of the 5-HT2C receptor has allowed us to propose a novel primary binding interaction for this series of diaryl ureas, involving a potential double hydrogen-bonding interaction between the urea carbonyl oxygen of the ligand and two serine residues in the receptor. The difference of two valine residues in the 5-HT2C receptor for leucine residues in the 5-HT2A receptor is believed to account for the observed 5-HT2C/5-HT2A selectivity with 2.

  DOI：

  10.1021/jm960571v
• 作为产物：
  描述：

  2,3-二氯丙烯 、 1-乙酰基-5-氨基二氢吲哚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以92%的产率得到N-(1-acetyl-5-indolinyl)-2-chloroallylamine
  参考文献：
  名称：

  Synthesis, Biological Activity, and Molecular Modeling Studies of Selective 5-HT_2C/2B Receptor Antagonists

  摘要：

  The synthesis and biological activity are reported for a series of analogues of the previously published indole urea 2 (SB-206553), designed to probe the 5-HT2C receptor binding site. Small molecule modeling studies have been used to define a region in space which is allowed at the 5-HT2C receptor but disallowed at the 5-HT2A receptor. In a complementary approach, docking of 2 into our model of the 5-HT2C receptor has allowed us to propose a novel primary binding interaction for this series of diaryl ureas, involving a potential double hydrogen-bonding interaction between the urea carbonyl oxygen of the ligand and two serine residues in the receptor. The difference of two valine residues in the 5-HT2C receptor for leucine residues in the 5-HT2A receptor is believed to account for the observed 5-HT2C/5-HT2A selectivity with 2.

  DOI：

  10.1021/jm960571v

文献信息

• CONDENSED INDOLE DERIVATIVES AS 5HT 2C? AND 5HT 2B? ANTAGONISTS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0656003A1

  公开（公告）日：1995-06-07
• [EN] CONDENSED INDOLE DERIVATIVES AS 5HT2C AND 5HT2B ANTAGONISTS<br/>[FR] DERIVES D'INDOLE CONDENSES UTILISES COMME ANTAGONISTES DES RECEPTEURS 5HT2C et 5HT2B
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO1994004533A1

  公开（公告）日：1994-03-03

  (EN) Compounds of formula (I) or a salt thereof wherein: P represents a quinoline or isoquinoline residue, or a 5- or 6-membered aromatic heterocyclic ring containing up to three heteroatoms selected from nitrogen, oxygen or sulphur; R1 is hydrogen or C1-6 alkyl; R2, R3, R10 and R11 are independently hydrogen or C1-6 alkyl, or R10 and R11 together form a bond, or R2 and R10 or R3 and R11 together form a C2-6 alkylene chain; R4 is hydrogen, C1-6 alkyl, halogen, NR8R9 or OR12, where R8, R9 and R12 are independently hydrogen or C1-6 alkyl; R5 is hydrogen or C1-6 alkyl; R7 is hydrogen, C1-6 alkyl, OR12 or halogen, where R12 is hydrogen or C1-6 alkyl; n is 2 or 3; and the groups R13 and R14 are independently hydrogen or C1-6 alkyl, are 5HT2C/5HT2B receptor antagonists and are of potential use in the treatment of CNS disorders such as anxiety.(FR) Composés de formule (I) ou leur sel, formule dans laquelle P représente un résidu quinoléine ou isoquinoléine, ou bien un composé hétérocyclique aromatique pentagonal ou hexagonal renfermant jusqu'à 3 hétéroatomes choisis parmi azote, oxygène ou soufre; R1 est hydrogène ou alkyle C1-6; R2, R3, R10 et R11 sont indépendamment hydrogène ou alkyle C1-6, ou bien R10 et R11 forment ensemble une liaison, ou encore R2 et R10 ou R3 et R11 forment ensemble une chaîne alkylène C2-6; R4 est hydrogène, alkyle C1-6, halogène, NR8R9 ou OR12, où R8, R9 et R12 sont indépendamment hydrogène ou alkyle C1-6; R5 est hydrogène ou alkyle C1-6; R7 est hydrogène, alkyle C1-6, OR12 ou bien halogène, où R12 est hydrogène ou alkyle C1-6; n vaut 2 ou 3; et les groupes R13 et R14 sont indépendamment hydrogène ou alkyle C1-6. Ces composés sont des antagonistes des récepteurs 5HT2C/5HT2B et sont d'une utilisation potentielle dans le traitement des troubles du système nerveux central, tels que l'anxiété.
• Synthesis, Biological Activity, and Molecular Modeling Studies of Selective 5-HT_2C/2B Receptor Antagonists
  作者：Ian T. Forbes、Steven Dabbs、D. Malcolm Duckworth、Peter Ham、Graham E. Jones、Frank D. King、Damian V. Saunders、Frank E. Blaney、Christopher B. Naylor、Gordon S. Baxter、Thomas P. Blackburn、Guy A. Kennett、Martyn D. Wood

  DOI：10.1021/jm960571v

  日期：1996.1.1

  The synthesis and biological activity are reported for a series of analogues of the previously published indole urea 2 (SB-206553), designed to probe the 5-HT2C receptor binding site. Small molecule modeling studies have been used to define a region in space which is allowed at the 5-HT2C receptor but disallowed at the 5-HT2A receptor. In a complementary approach, docking of 2 into our model of the 5-HT2C receptor has allowed us to propose a novel primary binding interaction for this series of diaryl ureas, involving a potential double hydrogen-bonding interaction between the urea carbonyl oxygen of the ligand and two serine residues in the receptor. The difference of two valine residues in the 5-HT2C receptor for leucine residues in the 5-HT2A receptor is believed to account for the observed 5-HT2C/5-HT2A selectivity with 2.